Cyclopeptide and method for preparing the same
AssigneeNational Tsing Hua University
InventorsChien-Tien CHEN, Shiue-Shien WENG
Life of this patent
Estimating the term…
Abstract
A method for preparing a cyclopeptide and a cyclopeptide preparing by the method are disclosed. The method includes the following steps: (A) providing compounds represented by the following formulas (I-1) and (I-2): wherein, G, Ra, Rb, Rc, Rd, and Re are defined in the specification; (B) performing a reaction between the compounds of formulas (I-1) and (I-2) to obtain a compound represented by the following formula (I-3): and (C) performing a cyclization reaction of the compound of formula (I-3) with a catalyst of formula (II) and deprotection to obtain a compound represented by the following formula (III): wherein, G′, Q, M, L1, L2, m, y, and z are defined in the specification.
Claims30
A method for preparing a cyclopeptide, comprising the following steps:
- (A) providing compounds represented by the following formulas (I-1) and (I-2):
- wherein, Ra, Rb and Rc are each independently a protection group;
- Rc and Rd are each independently alkyl, cycloalkyl, aryl or heteroaryl;
- G is H, or O-t-Bu;
- and
- R1 is
- in which R2 and R3 are each independently H or C1-6 alkyl;
- X is O, S, CH2, or N—R4, in which R4 is H, C1-6 alkyl, (CH2CH2O)nH, —C(═O)—C1-15 alkyl, —C(═O)CH2(OC2H4)nOR′ or C(═O)(C2H4)2C(═O)O(C2H4O)nR′, in which n=1-3 and R′ is H or CH3;
- (B) performing a reaction between the compounds of formulas (I-1) and (I-2) to obtain a compound represented by the following formula (I-3):
- and
- (C) performing a cyclization reaction of the compound of formula (I-3) with a catalyst of formula (II) and deprotection to obtain a compound represented by the following formula (III):
- M(O)mL1yL2z (II)
- wherein G′ is H or OH;
- Q is halogen, OC(O)CF3 or OC(O)CH3;
- M is a metal selected from the group consisting of IVB, VB, VIB and actinide groups;
- L1 and L2 respectively is a ligand;
- m and y are integers greater than or equal to 1;
- and
- z is an integer greater than or equal to 0.
A method for preparing a cyclopeptide, comprising the following steps:
- (a) providing compounds represented by the following formulas (I-1) and (I-4):
- wherein, Ra, Rb and Rc are each independently a protection group;
- Rc and Rd are each independently alkyl, cycloalkyl, aryl or heteroaryl;
- G is H or O-t-Bu;
- and
- R1 is
- in which R2 and R3 are each independently H or C1-6 alkyl;
- X is O, S, CH2, or N—R4, in which R4 is H, C1-6 alkyl, (CH2CH2O)nH, —C(═O)—C1-15 alkyl, —C(═O)CH2(OC2H4)nOR′ or C(═O)(C2H4)2C(═O)O(C2H4O)nR′, in which n=1-3 and R′ is H or CH3;
- (b) performing a reaction between the compounds of formulas (I-1) and (I-4) to obtain a compound represented by the following formula (I-5):
- (c) performing a reaction between the compound of formula (I-5) and the compound represented by the following formula (I-6) to obtain a compound represented by the following formula (I-7):
- wherein Rf is alkyl, cycloalkyl, aryl, or heteroaryl;
- and
- (d) performing a cyclization reaction of the compound of formula (I-7) with a catalyst of formula (II) and deprotection to obtain a compound represented by the following formula (III):
- M(O)mL1yL2z (II)
- wherein G′ is H or OH;
- Q is halogen, OC(O)CF3, or OC(O)CH3;
- M is a metal selected from the group consisting of IVB, VB, VIB and actinide groups;
- L1 and L2 respectively is a ligand;
- m and y are integers greater than or equal to 1;
- and
- z is an integer greater than or equal to 0.
A cyclopeptide represented by the following formula (III):
- wherein G′ is H or OH;
- Q is halogen, OC(O)CF3 or OC(O)CH3;
- and
- R1 is
- in which R2 and R3 are each independently H or C1-6 alkyl;
- X is O, S, CH2, or N—R4, in which R4 is H, C1-6 alkyl, (CH2CH2O)nH, —C(═O)—C1-15 alkyl, —C(═O)CH2(OC2H4)nOR′ or C(═O)(C2H4)2C(═O)O(C2H4O)nR′, in which n=1-3 and R′ is H or CH3.
Dependencies are inferred from the claim text.